One-pot efficient synthesis of novel fused pentacyclic indolopyridobenzimidazoles and pyridoimidazopyridoindoles from the reaction of pyranoindolones with 1,2-diaminobenzenes and 2,3-diaminopyridines

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• 作者：Despina Livadiotou ; Anna Maria Fadel ; Constantinos A. Tsoleridis ; Julia Stephanidou-Stephanatou ; ^{ioulia@chem.auth.gr}
• 关键词：Bisnucleophiles ; o-Phenylenediamines ; 2 ; 3-Diaminopyridines ; Indolopyridobenzimidazoles ; Pyranoindolones
• 刊名：Tetrahedron
• 出版年：2012
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：3 June, 2012
• 卷：68
• 期：22
• 页码：4202-4209
• 文件大小：737 K

摘要

The synthesis of a number of novel, fully conjugated, planar pentacyclic 5H-indolo[3鈥?2鈥?4,5]pyrido[1,2-a][1,3]benzimidazoles (ong class="boldFont">8ong>) and 11H-pyrido[3鈥?2鈥?4鈥?5鈥瞉imidazo[1鈥?2鈥?1,6]pyrido[3,4-b]indoles (ong class="boldFont">12ong>) by a one-pot reaction of pyranoindolones with substituted o-phenylenediamines or 2,3-diaminopyridines is described. In the case of 2,3-diaminopyridines the reaction proceeds regioselectively affording only regioisomers ong class="boldFont">12ong>. Structural assignments of the new compounds as well as complete assignment of ¹H and聽¹³C NMR signals were based on the analysis of their ¹H and ¹³C NMR (1D and 2D), IR, MS and elemental analysis data. Plausible mechanisms are proposed.